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Florence and Radda in Chianti (Self Drive)
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7 to 10+ Nigths from $1,359*
This sample price: priced within the past 7 days for arrival on 8/17/2025, departure from New York City NYC (All Airports) (NY), US. Choose your own departure city, cabin type and dates.
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1 Customer Feedbacks Hotels were great, transportation okay, tours were fair, and your services excellent. One ... more
This is a suggested independent itinerary that you customize. Please select the best flights, hotels, trains, activities, transportation and number of nights in each destination to fit your needs.
Charming trip to central Tuscany from Italy!. Visit the magnificent city of Florence (capital of Italy’s Tuscany region, is home to many masterpieces of Renaissance art and architecture) and after that, rent a car and spend a few days at your leisure in Radda in Chianti (a comune in the Province of Siena in the Italian Tuscany, a beautiful medieval town enclosed in large defensive walls). Drive back to Florence to drop off the car and finisht this trip with one last night stay. This is a flexible vacation package. Select your number of nights in each city, desired hotel and activities.
This 7 night sample itinerary includes:
  • Flight into and out of Florence
  • Hotel for 3 nights in Florence
  • Rental Car for 5 days
  • Hotel for 3 nights in Radda in Chianti
  • Hotel for 1 night in Florence

  • Driving Time
    Florence - Radda in Chianti : 1 hr. 10 mins. approx.
    Radda in Chianti - Florence: 1 hr. 10 mins. approx.

Price history for this itinerary (past 7 days):
From New York City NYC (All Airports) (NY), US for 7 nights
1358.75 * incl.tax
Related Itineraries:
Related Cities:
Florence (222)     Chianti Wine Region (11)     Radda in Chianti (1)    
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1. Florence
  284 hotels
2. Radda in Chianti
   (9 hotels)
3. Florence
   (284 hotels)
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Please contact us for any special arrangements such as more than three rooms and partial stays.
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Trip Summary
3 nights in Florence

The city of Florence sits nestled among the rolling Tuscan hills, with an unmistakable skyline dominated by the fabulous Duomo. With so much Renaissance art and culture, shopping opportunities, and incredible culinary delights, you will be spoiled for choices in what to do and see in this exciting capital city of Tuscany. Florence's museums, palaces, and churches house some of the greatest artistic treasures in the world.

Visit The Duomo Complex, Church of Santa Croce, The Cathedral, The Uffizi Gallery, Galleria dell'Accademia, Ponte Vecchio, Palazzo Vecchio, Pitti Palace, Boboli Gardens and so much more.



3 nights in Radda in Chianti

Located on a hilltop, covered with woods and extensive vineyards, between the valleys of Arbia and Pesa, Radda in Chianti is a beautiful medieval town enclosed in large defensive walls. The town retains its narrow medieval streets that meet in the main square where you'll find the Church of San Niccolo, from the 14th century, and the Palazzo Pretorio, built about 1415. The town has been the head of the League of Chianti since 1415. Just outside the village, in the Vignale farm, are the headquarters of the Chianti Classico consortium and the Centro di Studi Chiantigiani (Centre for Chianti Studies), founded in 1984, with a small library and an archive devoted to the history of Chianti and its agriculture.

Discover and explore the Castelo di Volpaia Winery, Fattoria di Montemaggio, Brancaia Winery, Castello di Radda, Cantina Castelvecchi in Chianti and so much more.



1 nights in Florence

The city of Florence sits nestled among the rolling Tuscan hills, with an unmistakable skyline dominated by the fabulous Duomo. With so much Renaissance art and culture, shopping opportunities, and incredible culinary delights, you will be spoiled for choices in what to do and see in this exciting capital city of Tuscany. Florence's museums, palaces, and churches house some of the greatest artistic treasures in the world.

Visit The Duomo Complex, Church of Santa Croce, The Cathedral, The Uffizi Gallery, Galleria dell'Accademia, Ponte Vecchio, Palazzo Vecchio, Pitti Palace, Boboli Gardens and so much more.



Book This Package
Flexible Itinerary
Florence
Day 1
Arrive to Florence
Overnight in Florence   284 hotels offered
Optional   1346 Things to do
Day 2
Overnight in Florence   284 hotels offered
Optional   1346 Things to do
Day 3
Overnight in Florence   284 hotels offered
Optional   1346 Things to do
Day 4
Departing from Florence
Transportation to next city by: Regional Air
Radda in Chianti
Day 4
Arrive to Radda in Chianti
Overnight in Radda in Chianti   9 hotels offered
Day 5
Overnight in Radda in Chianti   9 hotels offered
Day 6
Overnight in Radda in Chianti   9 hotels offered
Day 7
Departing from Radda in Chianti
Transportation to next city by: Regional Air
Florence
Day 7
Arrive to Florence
Overnight in Florence   284 hotels offered
Optional   1346 Things to do
Day 8
Departing from Florence
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Florence Hotels (284 total)
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Radda in Chianti Hotels (9 total)
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Tours in Florence (1346 total)
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Italy

For centuries <b>Italy</b> has drawn foreign visitors - mostly for its architectural, artistic, and scenic splendors. Italy can truly be all things to all people. From the passion and excitement of noisy urban crowds to the quiet, rural idyll where the traditional life can be experienced, Italy's great cities are replete with rich attractions and culture alongside some of the most pristine beaches and spectacular mountains in the world.
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Price Guidance

The package rates displayed are your total price per person based on Double Occupancy and your Arrival Date and Number of Nights selected. You can change details after selecting your travel date.

Price history for this itinerary (past 7 days):

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*Sample prices on display include ALL taxes & fuel surcharges... read more
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Florence and Radda in Chianti (Self Drive)
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Florence
The city of Florence sits nestled among the rolling Tuscan hills, with an unmistakable skyline dominated by the fabulous Duomo. With so much Renaissance art and culture, shopping opportunities, and incredible culinary delights, you will be spoiled for choices in what to do and see in this exciting capital city of Tuscany. Florence's museums, palaces, and churches house some of the greatest artistic treasures in the world.

Visit The Duomo Complex, Church of Santa Croce, The Cathedral, The Uffizi Gallery, Galleria dell'Accademia, Ponte Vecchio, Palazzo Vecchio, Pitti Palace, Boboli Gardens and so much more.
Radda in Chianti
Located on a hilltop, covered with woods and extensive vineyards, between the valleys of Arbia and Pesa, Radda in Chianti is a beautiful medieval town enclosed in large defensive walls. The town retains its narrow medieval streets that meet in the main square where you'll find the Church of San Niccolo, from the 14th century, and the Palazzo Pretorio, built about 1415. The town has been the head of the League of Chianti since 1415. Just outside the village, in the Vignale farm, are the headquarters of the Chianti Classico consortium and the Centro di Studi Chiantigiani (Centre for Chianti Studies), founded in 1984, with a small library and an archive devoted to the history of Chianti and its agriculture.

Discover and explore the Castelo di Volpaia Winery, Fattoria di Montemaggio, Brancaia Winery, Castello di Radda, Cantina Castelvecchi in Chianti and so much more.
Florence
The city of Florence sits nestled among the rolling Tuscan hills, with an unmistakable skyline dominated by the fabulous Duomo. With so much Renaissance art and culture, shopping opportunities, and incredible culinary delights, you will be spoiled for choices in what to do and see in this exciting capital city of Tuscany. Florence's museums, palaces, and churches house some of the greatest artistic treasures in the world.

Visit The Duomo Complex, Church of Santa Croce, The Cathedral, The Uffizi Gallery, Galleria dell'Accademia, Ponte Vecchio, Palazzo Vecchio, Pitti Palace, Boboli Gardens and so much more.

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